Biodegradation of [14C] Ring-Labeled Nonylphenol Ethoxylate

Nonylphenol (NP) and the 9-mole ethoxylate of nonylphenol (NPE9) were synthesized with a uniform radioactive 14C label in the aromatic ring. The [14C]NP isomer distribution and [14C]NPE9 oligomer distribution closely matched that of commercial NPE9. Biodegradation of [14C]NPE9 was examined under conditions simulating a river water environment, and changes in the oligomer distribution and mineralization to 14CO2 were monitored for 128 days. Over 40% of the [14C]NPE aromatic ring carbon was converted to 14CO2 and another 21% was incorporated into the biomass. Primary degradation of NPE (conversion to metabolites other than NP, NPE ethoxylates, and NPE carboxylates) was estimated to be 87–97%. NP was a minor metabolite, accounting for less than 0.4% of the initial NPE. These studies demonstrate that the phenolic ring of NPE is opened, metabolized, and mineralized in the aquatic environment.

[1]  R. Düring,et al.  Sorption behavior of nonylphenol in terrestrial soils. , 2002, Environmental science & technology.

[2]  G. F. White,et al.  Biodegradation of surfactants , 1995 .

[3]  B. Thiele,et al.  Alkylphenol Ethoxylates: Trace Analysis and Environmental Behavior. , 1997, Chemical reviews.

[4]  D. Bennie.  Review of the environmental occurrence of alkylphenols and alkylphenol ethoxylates , 1999 .

[5]  W. Giger,et al.  Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment—I. Occurrence and transformation in sewage treatment , 1994 .

[6]  R. Maguire.  Review of the Persistence of Nonylphenol and Nonylphenol Ethoxylates in Aquatic Environments , 1999 .

[7]  U. Zoller.  Handbook of Detergents - Part B: Environmental Impact , 2007 .

[8]  C. Naylor.  The Environmental Fate and Safety of Nonylphenol Ethoxylates , 1996 .

[9]  M. Reinhard,et al.  Occurrence and fate of pharmaceuticals and alkylphenol ethoxylate metabolites in an effluent‐dominated river and wetland , 2004, Environmental toxicology and chemistry.

[10]  R. Kookana,et al.  Environmental fate of alkylphenols and alkylphenol ethoxylates--a review. , 2002, Environment international.

[11]  P. Dillon,et al.  Sorption and degradation of selected five endocrine disrupting chemicals in aquifer material. , 2003, Water research.

[12]  K. Bock.  Surfactant Biodegradation, Surfactant Science Series Vol. 3. Von R. D. Swisher. Marcel Dekker, Inc., New York 1970. XXIII, 496 S., geb. $ 33.50 , 1971 .

[13]  K. Yoshimura.  Biodegradation and fish toxicity of nonionic surfactants , 1986 .

[14]  K. E. Simmons,et al.  Static die-away of a nonylphenol ethoxylate surfactant in estuarine water samples , 1999 .

[15]  A. Bergman,et al.  Biodegradation of 4-nonylphenol in seawater and sediment. , 1993, Environmental pollution.

[16]  Kazuichi Hayakawa,et al.  Photodegradation of 4-alkylphenols using BiVO4 photocatalyst under irradiation with visible light from a solar simulator , 2003 .

[17]  J. Williams,et al.  Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol. , 1999, Chemosphere.

[18]  C. Naylor,et al.  Trace analysis of alkylphenol ethoxylates , 1990 .

[19]  S. Valsecchi,et al.  Determination of 4-nonylphenol and 4-nonylphenol ethoxylates in river sediments by microwave assisted solvent extraction. , 2003, Annali di chimica.

[20]  C. Crescenzi,et al.  Occurrence and abundance of dicarboxylated metabolites of nonylphenol polyethoxylate surfactants in treated sewages , 2000 .

[21]  Klaus Guenther,et al.  Endocrine disrupting nonylphenols are ubiquitous in food. , 2002, Environmental science & technology.

[22]  J. Lech,et al.  Metabolism of several 14C-nonylphenol isomers by rainbow trout (Oncorhynchus mykiss): in vivo and in vitro microsomal metabolites. , 1996, Xenobiotica; the fate of foreign compounds in biological systems.

[23]  K. Guenther,et al.  Contribution to the structural elucidation of 10 isomers of technical p-nonylphenol. , 2004, Environmental science & technology.

[24]  W. E. Gledhill,et al.  Ultimate biodegradation of alkylphenol ethoxylate surfactants and their biodegradation intermediates , 2001, Environmental toxicology and chemistry.

[25]  J. Lech,et al.  Uptake, disposition, and persistence of nonylphenol from water in rainbow trout (Oncorhynchus mykiss). , 1996, Xenobiotica; the fate of foreign compounds in biological systems.

[26]  A. Marinoni,et al.  Characterization of Recalcitrant Intermediates from Biotransformation of the Branched Alkyl Side Chain of Nonylphenol Ethoxylate Surfactants , 1998 .

[27]  Scott W. Pryor,et al.  Nonylphenol in anaerobically digested sewage sludge from New York State. , 2002, Environmental science & technology.

[28]  M. E. Gill,et al.  Estrogenic alkylphenols in fish tissues, sediments, and waters from the U.K. Tyne and Tees estuaries , 1999 .

[29]  E. Funari,et al.  Alkylphenolic compounds in edible molluscs of the Adriatic Sea (Italy). , 2001, Environmental science & technology.

[30]  R. Maguire,et al.  ALKYLPHENOL POLYETHOXYLATE METABOLITES IN CANADIAN SEWAGE TREATMENT PLANT WASTE STREAMS , 1998 .

[31]  N. Coldham,et al.  Biotransformation, tissue distribution, and persistence of 4-nonylphenol residues in juvenile rainbow trout (Oncorhynchus mykiss). , 1998, Drug metabolism and disposition: the biological fate of chemicals.

[32]  Todd F. Wheeler,et al.  Mass Spectral Characterization of p-Nonylphenol Isomers Using High-Resolution Capillary GC—MS , 1997 .

[33]  T. Ford.  Aquatic microbiology : an ecological approach , 1995 .

[34]  J. Field,et al.  Nonylphenol polyethoxy carboxylate metabolites of nonionic surfactants in U.S. paper mill Effluents, Municipal sewage treatment plant effluents, and river waters , 1996 .

[35]  C. Naylor,et al.  Environmental fate of alkylphenol ethoxylates , 1992 .

[36]  W. Ding,et al.  Analysis of nonylphenol polyethoxylates and their degradation products in river water and sewage effluent by gas chromatography-ion trap (tandem) mass spectrometry with electron impact and chemical ionization. , 1998, Journal of chromatography. A.

[37]  J. Loyo-Rosales,et al.  A simple method for the determination of trace levels of alkylphenolic compounds in fish tissue using pressurized fluid extraction, solid phase cleanup, and high-performance liquid chromatography fluorescence detection. , 2002, Journal of agricultural and food chemistry.